


And So They Thought Back... and Thought "What If?"

by luvtheheaven



Category: Gilmore Girls
Genre: F/M
Language: English
Status: In-Progress
Published: 2014-04-03
Updated: 2014-04-03
Packaged: 2018-01-18 01:06:46
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,414
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1409332
Author URL: https://archiveofourown.org/users/luvtheheaven/pseuds/luvtheheaven
Summary: <blockquote class="userstuff">
              <p>Lorelai & Luke's wedding is approaching, and Rory & Jess both are forced to think back to so many of the things in their relationship that could have and maybe should have gone differently. Takes a bunch of canon moments and twists them into totally different AU scenarios via them thinking "what if?" - basically each what if *could* be the basis of an entire fic that shoots off in an AU direction, but instead I keep them short and simple so that I can cover a lot more of the many ideas going through my head for my favorite ship. ;)</p>
            </blockquote>





	And So They Thought Back... and Thought "What If?"

**Author's Note:**

> I know Luke & Lorelai's wedding has been done 50 million times in Literati fanfic world btw, but let me have my chance to do it too, please? I promise to try to be unique and my fic really isn't gonna focus on the wedding much. You'll see as I keep writing it. And thank you to Iscah_McKrae over at fanfiction.net for being my beta/helping me come up with this whole fic idea in the first place. She's the best, and she's an insanely talented Gilmore Girls fanfic writer herself. Also, I wrote this first chapter in July 2012 but I still have not given up on the idea of posting a chapter 2 (and many more chapters) sometime. ;) I hope I will.

Chapter 1: As the Wedding Approaches...

Rory hesitantly stepped out of the dressing room and into Lorelai's line of sight. Clearly, her mother was pleased with this dress, for the smile that quickly stretched from ear to ear on her face was a reaction of sheer happiness, so infectious that Rory couldn't help but smile back in return.

"Mom, you're not supposed to like the very first dress I try on _quite_ this much," she said with a slight air of amusement. "And if you like it too much," she added, "then it's probably a bad thing because that means I'm gonna be detracting from _you_ being the center of attention!"

"Nonsense!" Lorelai countered, completely unfazed by her daughter's concerns. "This dress is too perfect to pass up and if people want to look at you on my wedding day, then... whatever. You're half my genes and even more my personality, so it's kinda like they're looking at me – in a way. You know?"

Rory rolled her eyes and smiled, then took a look at herself in a mirror. The dress was pretty gorgeous. It was a shade of bright light blue that reminded her of the sky, but with silver fringe sparkling in just the right places. It was fairly simple and elegant but possessed just enough "flair" that it was clearly fancy and meant for an extra special occasion – not the kind of thing she would have worn to Friday night dinner at Emily and Richard's house, for example. Rory admired the stitching, thinking how much more she liked this dress than probably every dress she had ever worn over to her grandparents' house those evenings. She twirled a bit and felt just like a princess. She was really glad that her mom was willing to buy such an expensive dress for her, since she was pretty much broke at the moment. The Obama campaign was a great experience, in so many ways... but it had paid so little; now that it was over she needed to use all of that money to pay rent for her new apartment and to buy the bare necessities of life until she landed another job. Lorelai and Luke had purposely scheduled their wedding on a date when Rory would be finished reporting for the campaign. However they had left Rory only a week to prepare for it, so she had no time to go interview for a new job yet - not when she had all the standard maid of honor duties, including dress shopping, to do.

"Honey, every woman at this wedding is gonna be so jealous of you!" Lorelai gushed, positively giddy over the beautiful dress. She walked right up behind Rory as Rory continued to consider her reflection. "You know it's perfect, right? You don't need to try on another one, I swear."

Rory thought about what her mother just said. Every woman would be jealous. But what about the men? She couldn't help but wonder. What would they think when they saw her? She wasn't thinking of the groom, although, if his thoughts weren't understandably otherwise occupied, Luke would probably be taken aback at how... stunning... the Rory he knew looked in such a dress. She also wasn't thinking of the average male friend or acquaintance of Lorelai that may have been invited, like Jackson or Kirk. No. Rory's mind couldn't help but jump to Jess. He was Luke's nephew. Lorelai hadn't mentioned anything about Jess coming... but Rory knew Jess would _have_ to be at Luke's wedding. After all, Luke had been Jess' guardian for two years of high school. Luke had come to his open house. Of course Luke, who had little family and few close friends _other_ than Jess, would want Jess at his wedding.

Rory wasn't sure why it should matter what Jess did or didn't think when he saw her at the wedding. She was over him. In fact it had been so long since they were actually dating that Rory had practically lost count of how many years had passed. High school felt like another lifetime to her, now that she had graduated from college and worked out in the real world, traveling the whole country. Since then, she'd dated Dean again, and had her whole relationship with Logan. Sure, a bit more recently in Truncheon Books they'd kissed, but it had been nothing, Rory reasoned. _He_ kissed _her_. _She_ had still been fully in love with Logan then, and just cared about Jess in a platonic way, regardless of what he may have been feeling.

Still, she couldn't help but think about the first bridesmaid's dress she'd ever worn. It was teal. Sookie's wedding. She could still remember how he looked at her in that simple dress. She could still hear his voice... the innocent, sweet Jess voice that he'd seemed to save for her. "You look nice." That was back before everything had really started - before their whole tumultuous romance. She couldn't help but wonder if he might still have feelings for her now. Did she want him to? That was ridiculous. Of course not. But at the same time, she still wasn't sure if she wanted Jess to have "moved on" from her forever.

A part of Rory really liked the idea of Jess being stunned by her appearance. More than that, she liked the idea of him seeing her at the wedding and feeling his eyes skim over her body, seeing him bite his lower lip, and knowing what he was thinking... She made a small movement like she was jerking herself awake. It terrified her to realize she had these thoughts - that the idea of seeing an ex-flame would make her mind go there. But she couldn't dismiss the idea.

Rory took a deep breath to snap out of her Jess-centric thoughts, remembering that back in reality she was taking quite a while looking in the mirror at herself. She turned around, looked back into her mother's eyes, and smiled.

"You're right. Normally I'd... try on some more dresses first, just to be sure... maybe do a pro/con list about the dresses even," she added with half a laugh. "But this dress seems too good to be true. I really do want this one."

Lorelai squealed in response and then immediately started pushing her daughter back into the dressing room.

"Yay! Now please take it off, so that I can pay for it before you change your mind!"

Rory closed the dressing room door behind her and latched it shut, then stripped back down to her bra and panties. She looked back at her nearly naked body in the mirror and again her thoughts began to drift... He'd never seen her this way. Both Dean and Logan had... but not Jess. It was strange. There were so many things she and Jess had never done that at the time she was so sure they would do. So many things that never happened between them, that never were said, that turned out differently than she'd expected. And as she stood there, lost in thought... her mind went back to the very beginning of her relationship with Jess... and even to before the very beginning... and she thought "what if?".

* * *

Jess was heading to 15th St. Trolley Station by foot. He was thankful that his apartment, Truncheon Books, and even the train station that could take him to Hartford, Connecticut were all in such convenient locations within the city of Philadelphia that he could get to pretty much all of the places that he ever needed to go by simply walking.

He was prepared to write as much as he could on the five to six hour train ride to Hartford, because once he arrived and Luke picked him up and drove him back to Stars Hollow, Jess anticipated being unable to find any more free time for writing. Luke had asked asked him to be the best man at his wedding, and while Jess actually wasn't that surprised that he'd been chosen for the role, he also wasn't quite sure what he should do in order to fill it. Luke wasn't the kind of guy to want to head off to a strip club and get wasted at a bachelor party that Jess could potentially throw him like the typical best man might in a cheesy TV movie. He then smirked, remembering how Luke had refused a lap dance at that mud wrestling joint.

However Jess did anticipate needing to do _something_ when he got there that was in preparation for the wedding. For his mother's weddings all he'd had to do was show up dressed appropriately – usually something barely nicer than what he wore every day was fine, but then most recently there was the Renaissance themed one. Jess smirked to himself, thinking back to the ridiculous costumes everyone there was wearing, thankful that a loose-fitting yellow shirt was the worst he'd gotten stuck with.

Jess had never attended any weddings other than his mother's, and he found himself oddly excited to be going to one for someone else. Someone that he felt truly happy for, in a way he'd never been able to fully feel for his own mother. He had always wanted Liz to be happy, sure, but the weddings never felt right for her, and it just was somehow very different with Luke. Luke was such a sweet and simple guy. He did everything for everybody. And often, he seemed so lonely. Luke deserved this, and regardless of how pessimistic about love he usually was these days, Jess found himself feeling quite confident that this marriage was something that would work out in the long run. He had an unusual amount of faith that this would make not only Luke, but also Lorelai truly happy.

Lorelai... Jess sighed. Thinking about Lorelai made him think about the fact that Rory would be at the wedding too. She couldn't _not_ be Lorelai's maid of honor. Naturally, this had crossed Jess' mind an innumerable number of times since he'd been invited to be a member of the wedding party. He usually tried his best to just think of it as a simple fact and not consider what he actually felt about it. He didn't usually let himself consider what the implications of Rory's presence would be... where she would be... the things they'd inevitably be expected to do together. But today, walking down the streets of Philadelphia, he found himself finally letting his mind go there.

He didn't know much about Rory and her life right now. He figured Luke would've mentioned if she'd gotten married or had a baby, or done something particularly noteworthy like that. But then again, Luke seemed to avoid talking about Rory in his brief conversations with Jess. He had seemed so hesitant to even let Jess be privy to Rory's whereabouts back when _The Subsect_ had first been published. Jess hadn't actually found out anything new about Rory since that fateful night at Truncheon – he didn't even know if she'd graduated college successfully although, deep down, he knew that she had; it was too impossible for someone as smart and driven as her to fail.

At the same time, though, Rory had been so in love with that Logan jerk that she'd even taken him back after he'd cheated on her, as much as Jess hated to believe it. He couldn't understand how Rory could fall for someone who was so clearly wrong for her in almost every way. He was a rich snob who didn't seem to have a shred of common decency in his blood, judging from the single hour Jess had spent in his company. (Plus of course the knowledge that he'd cheated on Rory – something Jess could never fathom doing in a million years.) But maybe Rory really wasn't the girl he'd fallen in love with when they were in high school. Maybe things had changed a lot and maybe she was _still_ with this dick because he was truly "the love of her life". Jess wasn't sure he could handle seeing Rory bring the piece of scum as her date to the joyous occasion. Jess might not be able to resist the urge to just punch him right in the face. Yeah - 'cause _that_ wouldn't ruin the joyous occasion or anything. He rolled his eyes. Of course for Luke's sake he'd be able to resist. He wondered if Rory had ever told Logan that she and Jess had "done something" in order to get revenge for him cheating on her. Maybe Logan would be at the wedding and would want to punch _Jess_ the moment their paths crossed!

Jess figured there was no point in worrying. He had to be at this wedding – there was no way his unresolved feelings for Rory could justify not being there for his uncle on such an important day of his life. And whatever would happen would happen; there was nothing he could really do except try to remain calm and detached about whatever he found out about Rory and her life. He could force a polite smile perhaps if they caught each other's eyes, and he could maybe even make a slight effort to avoid situations where that would happen. But that was about it. Their relationship had been done for good as soon as Rory had told him over the phone that she wasn't going to pine for him. There was no point in pretending there was any chance anymore for them to get back together. Even if Jess felt unable to ever imagine a time in his life when he'd fall in love again with someone new, he was resolved to living the rest of his life alone if he had to. He was past the point of having any real hope that Rory could ever be a part of his life again.

Still, Jess couldn't help but think about just how different things would be if there _was_ a chance. Rory could have pined for him the way he did for her. There were so many things both of them could have done differently, or things in their lives that could have gone differently. Jess walked through the doors of the station, and as he headed toward the ticket counter, he couldn't help but think of everything that could have been...so many possibilities... so many... "what if"s.

**Author's Note:**

> I have only one fic that I've written and posted to fanfiction.net but cannot post here on AO3. It is a songfic I wrote about Rory & Jess (a oneshot based on a song) - it quoted the lyrics of "Dear John" by Taylor Swift heavily, and is called "Don't You Think I Was Too Young?". I'd love it if you guys checked it out: https://www.fanfiction.net/s/6796959/1/Don-t-You-Think-I-Was-Too-Young - I am telling you about it here, because this fic is my only other exclusively Rory & Jess fic. I did have it posted here on AO3 for a time, but then AO3 emailed me about a copyright complaint. They told me the fic violated their site policy. Oh well. I think that's ridiculous. Other sites have the lyrics of the song: http://www.azlyrics.com/lyrics/taylorswift/dearjohn.html And all I did was the same basic thing. I never claimed they were my own writing. But whatever.


End file.
